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I like this map and would ask that the roads and trails be placed below the tree canopies. It would lend a more natural feel the the piece, and you may have to reshape some of the trees in order to see enough of the roads to be able to see that they are conected. Do you have plans to add any notes or a makers mark?

Yeah I didn't like how when I merged the layers the roads cut through the trees. On the next one I was wondering if I should put smaller trees near roads/trails to make them visible without cut through the trees. Hadn't really given it any thought about notes or makers mark

I would be inclined to tell you to use much smaller trees for the whole thing. As it is, though, I can't honestly say that I like it. It's very confusing. I'm not sure what the flat gray represents, but it cuts off awkwardly. I can't see any rhyme or reason to why the gray is where it is, and isn't where it isn't. And I would suggest giving your items either a degree of transparency or a blend mode that lets some of the texture show through. Because as it is, there is a textured background, but everything on top of it is totally flat.

It'll look better if all your tree symbols are the same size. In general, you don't want to be resizing elements hither and yon - the scale they were drawn at will make tree match mountain match city, and suchlike. If you decide the mountains should look big and imposing, and you just scale them up, it'll look subtly wrong. The little building symbols have been scaled down compared to mountains and trees, so their lineweight almost disappears.

Further, it's contributing to the confusion S_H notes, for you to have all those different tree symbols thrown together. Yes, a real forest has a variety of species. But a mapped forest is going to make more sense with less variety. If you need to show a pine forest as distinct from one of elms and oaks, fine - but stick with generic conifers first and generic deciduous for the other. Less 'exact' but a more usable map. Only if you're a botanist will you want to show all the applicable species and their spatial distribution.

Any map is going to need some generalization, and few are intended to be realistic to-scale aerial views. Okay, so the mountains are big - I get that. But their size is making me think the whole island is at most ten to thirty miles across. The sizes of the trees make me think it's about a mile across. The spacing of the settlements would indicate maybe tens to hundreds of miles across. 'Course you can settle all that by actually putting in a scale bar, but you get the point about appropriate symbol size?

If the gray is intended to be 'sketched in' ocean, and you're just not finished, maybe I can offer an example of an ocean-surrounding look that works (worked for me, anyway).

I'll use that as a BAD example on other aspects -- the discrepancy between my coastal linework and that of the cities/hills is worse than yours. And the labels should be way smaller (my excuse there was I was hand-lettering and compositing digitally, and I couldn't letter any smaller!).

You have a river problem at Sundyr Lake - it could have multiple inlets, but should have only one outlet. There's an absolutely golden tutorial on How To Get Your Rivers In The Right Place that will make sense of that for you.

There's a general problem we all have when we're trying to get a hand-drawn look, yet are relying on digital fonts. Imagine how your presumed olden cartographer drew this up. Those neat halos around the text work for legibility, but they kinda kill the period feel - how would the guy create that effect by hand? If he were REALLY patient and cautious he might have composed the whole picture in pencil first, then when he inked in forests, say, he might just leave out trees where he was going to put a city name, but he would likely not draw slivers of symbols, leaving such neat halos. Or he might just letter right over the top of the symbology - plenty of maps did that.

If you were to change just one thing, I'd say getting the symbols in the same scale would be the most bang for your buck.